Which Is More Soluble in Hexane: Hexyl Ethanoate or Octanoic Acid?

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The discussion centers on the solubility of hexyl ethanoate versus octanoic acid in hexane. One participant argues that octanoic acid, with its longer hydrocarbon chain, should be more soluble. Another counters this by highlighting the potential for hydrogen bonding in octanoic acid, which may affect its solubility in hexane. The conversation also notes that octanoic acid is relatively soluble in water, suggesting its polar characteristics. Ultimately, the solubility comparison hinges on the balance between hydrocarbon chain length and intermolecular interactions.
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Which is more soluble in hexane, hexyl ethanoate or octanoic acid?

I'm thinking it's octanoic acid with the longer uninterrupted hydrocarbon chain, where as the ester's longest uninterrupted hydrocarbon chain is composed of six carbons. Is this correct? If not can you please explain why? Thanks.
 
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i'm thinking the hexyl ethanoate, mainly because the intermolecular hydrogen bonding that can occur with octanoic acid, which can go both ways (donor, acceptor). Not certain though. Octanoic acid is fairly soluble in water
 
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